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Pentaerythritol tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate)

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Pentaerythritol tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate
Names
Preferred IUPAC name 2,2-Bis({oxy}methyl)propane-1,3-diyl bis
Other names Anox 20, Irganox 1010, Dovernox 10
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.214.246 Edit this at Wikidata
EC Number
  • 229-722-6
PubChem CID
RTECS number
  • DA8340900
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C73H108O12/c1-65(2,3)49-33-45(34-50(61(49)78)66(4,5)6)25-29-57(74)82-41-73(42-83-58(75)30-26-46-35-51(67(7,8)9)62(79)52(36-46)68(10,11)12,43-84-59(76)31-27-47-37-53(69(13,14)15)63(80)54(38-47)70(16,17)18)44-85-60(77)32-28-48-39-55(71(19,20)21)64(81)56(40-48)72(22,23)24/h33-40,78-81H,25-32,41-44H2,1-24H3Key: BGYHLZZASRKEJE-UHFFFAOYSA-N
SMILES
  • CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)CCC(=O)OCC(COC(=O)CCC2=CC(=C(C(=C2)C(C)(C)C)O)C(C)(C)C)(COC(=O)CCC3=CC(=C(C(=C3)C(C)(C)C)O)C(C)(C)C)COC(=O)CCC4=CC(=C(C(=C4)C(C)(C)C)O)C(C)(C)C
Properties
Chemical formula C73H108O12
Molar mass 1177.655 g·mol
Appearance White solid
Melting point 110–125 °C (230–257 °F; 383–398 K)
Solubility in water <0.1 g/ml
Solubility in Acetone 0.75 g/ml
Solubility in Toluene 0.5 g/ml
Solubility in Methanol <0.1 g/ml
Hazards
GHS labelling:
Hazard statements H413
Precautionary statements P273, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Pentaerythritol tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate) is a chemical compound composed of four sterically hindered phenols linked through a pentaerythritol core. It is used as primary antioxidant for stabilizing polymers, particularly polyethylene and polypropylene.

Synthesis

Base catalysed Michael addition of methyl acrylate to 2,6-di-tert-butylphenol forms the intermediate butyl-phloretic ester. High temperature transesterification of this with pentaerythritol gives the final product. Driving this reaction to completion can be difficult and commercial samples often contain low levels of the tri-ester.

Properties

The linking of phenols together with pentaerythritol maintains their activity with greatly reduced volatility. This is important during the processing and molding steps where the plastic is heated to molten, typically several hundred degrees.

See also

References

  1. Vulic, Ivan; Vitarelli, Giacomo; Zenner, John M. (January 2002). "Structure–property relationships: phenolic antioxidants with high efficiency and low colour contribution". Polymer Degradation and Stability. 78 (1): 27–34. doi:10.1016/S0141-3910(02)00115-5.
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